Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom

Bertin, Matthew J.; Zimba, Paul V.; He, Haiyin; Moeller, Peter D.R.

doi:10.1016/j.tetlet.2016.11.062

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i

Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom

2016
By Bertin, Matthew J. ; Zimba, Paul V. ; He, Haiyin ; ...
Source: Tetrahedron Letters, 57(52), 5864-5867

[PDF-499.31 KB]

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Journal Title:

Tetrahedron Letters
Personal Author:

Bertin, Matthew J. ; Zimba, Paul V. ; He, Haiyin ; Moeller, Peter D.R.

Bertin, Matthew J. ; Zimba, Paul V. ; He, Haiyin ; Moeller, Peter D.R. Less -
NOAA Program & Office:

NOS (National Ocean Service) ; NCCOS (National Centers for Coastal Ocean Science)

NOS (National Ocean Service) ; NCCOS (National Centers for Coastal Ocean Science) Less -
Description:

NMR-guided fractionation of the lipophilic extract of Trichodesmium thiebautii filaments led to the isolation of a phenyl-containing chlorinated polyketide (1) and an alkyne-containing analog (2). Comparison of spectroscopic and spectrometric data of 1 with the data of the previously reported trichotoxin, strongly suggested that these metabolites were identical and supports a structural revision of trichotoxin and its designation as trichotoxin A. In addition, we report the isolation and characterization of the alkyne-containing analog trichotoxin B (2). Absolute configuration of 1 and 2 is proposed based on spectroscopic comparison to a close structural analog.
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Biochemistry Cyanobacteria Toxicology
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Tetrahedron Letters, 57(52), 5864-5867
DOI:

https://doi.org/10.1016/j.tetlet.2016.11.062
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urn:sha256:cd1a9076749f4e020a7b41640d9422a9445eee5fbb89efff5f4f98300e3aa59f
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